catena-Poly[[diaqua-(1,10-phenanthroline-κN,N')nickel(II)]-μ-1H-benzimidazole-5,6-dicarboxyl-ato-κN:O].

In the title complex, [Ni(C(9)H(4)N(2)O(4))(C(12)H(8)N(2))(H(2)O)(2)](n), the Ni(II) atom is hexa-coordinated by one N and one O atom from two different 1H-benzimidazole-5,6-dicarboxyl-ate ligands, two N atoms from one 1,10-phenanthroline ligand and two water mol-ecules. The flexible 1H-benzimidazole-5,6-dicarboxyl-ate ligands link the Ni(II) centres, forming an infinite zigzag chain parallel to [001]. The crystal packing is governed by inter-molecular hydrogen-bonding inter-actions of the O-H⋯O, N-H⋯O and C-H⋯O types.

Related literature

For background to 1H-benzoimidazole-5,6-dicarboxyl­ate complexes, see: Lo et al. (2007 ▶); Yao et al. (2008 ▶); Gao et al. (2008 ▶). For background to n class="Chemical">1,10-phenanthroline complexes, see: Chesnut et al. (1999 ▶).

Experimental

Crystal data

[Ni(C9H4N2O4)(C12n class="Species">H8N2)(H2O)2]

M = 479.09

Monoclinic,

a = 10.021 (2) Å

b = 16.980 (3) Å

c = 15.327 (5) Å

β = 129.09 (2)°

V = 2024.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.01 mm−1

T = 293 K

0.31 × 0.26 × 0.22 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.746, T max = 0.809

15765 measured reflections

3639 independent reflections

3195 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.09

3639 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.25 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019680/im2119sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019680/im2119Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C9H4N2O4)(C12H8N2)(H2O)2]	F(000) = 984
Mr = 479.09	Dx = 1.572 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3600 reflections
a = 10.021 (2) Å	θ = 1.4–28°
b = 16.980 (3) Å	µ = 1.01 mm−1
c = 15.327 (5) Å	T = 293 K
β = 129.09 (2)°	Block, blue
V = 2024.3 (9) Å3	0.31 × 0.26 × 0.22 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	3639 independent reflections
Radiation source: fine-focus sealed tube	3195 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω scans	θmax = 25.2°, θmin = 3.2°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −11→12
Tmin = 0.746, Tmax = 0.809	k = −20→20
15765 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.2141P] where P = (Fo2 + 2Fc2)/3
3639 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Ni1	0.55530 (3)	0.434786 (13)	0.82246 (2)	0.02591 (11)
O1	0.38387 (19)	0.10540 (8)	0.49825 (13)	0.0398 (4)
O1W	0.76448 (17)	0.50597 (8)	0.94690 (12)	0.0318 (3)
H1W	0.7283	0.5441	0.9617	0.048*
H2W	0.8137	0.4736	1.0003	0.048*
O2	0.27333 (18)	0.22040 (9)	0.41361 (14)	0.0456 (4)
O2W	0.39504 (19)	0.49621 (9)	0.84828 (13)	0.0395 (4)
H3W	0.4521	0.5341	0.8920	0.059*
H4W	0.3796	0.4618	0.8805	0.059*
O3	0.59904 (17)	0.14247 (8)	0.43858 (11)	0.0314 (3)
O4	0.86749 (19)	0.10944 (10)	0.58603 (13)	0.0479 (4)
N1	0.7201 (2)	0.37301 (10)	0.80627 (14)	0.0296 (4)
N2	0.9708 (2)	0.34131 (11)	0.84962 (15)	0.0357 (4)
H2	1.0793	0.3421	0.8837	0.043*
N3	0.3234 (2)	0.38391 (10)	0.68890 (14)	0.0334 (4)
N5	0.4878 (3)	0.51071 (11)	0.69453 (16)	0.0407 (4)
C1	0.5577 (2)	0.22029 (11)	0.58394 (16)	0.0259 (4)
C2	0.7187 (2)	0.20098 (11)	0.61273 (16)	0.0277 (4)
C3	0.8679 (2)	0.23640 (12)	0.70388 (17)	0.0300 (4)
H3	0.9750	0.2227	0.7257	0.036*
C4	0.8508 (2)	0.29313 (12)	0.76130 (16)	0.0288 (4)
C5	0.6930 (2)	0.31336 (11)	0.73392 (16)	0.0261 (4)
C6	0.5439 (2)	0.27566 (11)	0.64394 (17)	0.0273 (4)
H6	0.4378	0.2875	0.6248	0.033*
C7	0.8876 (3)	0.38666 (13)	0.87258 (18)	0.0355 (5)
H7	0.9419	0.4241	0.9296	0.043*
C8	0.3932 (2)	0.17945 (12)	0.48969 (17)	0.0296 (4)
C9	0.7307 (2)	0.14601 (11)	0.54114 (17)	0.0297 (4)
C10	0.2431 (3)	0.32210 (15)	0.6884 (2)	0.0456 (6)
H10	0.2925	0.2953	0.7554	0.055*
C11	0.0856 (3)	0.29550 (19)	0.5899 (3)	0.0632 (8)
H11	0.0322	0.2514	0.5915	0.076*
C12	0.0117 (3)	0.33512 (19)	0.4919 (2)	0.0622 (8)
H12	−0.0927	0.3178	0.4263	0.075*
C13	0.0909 (3)	0.40118 (17)	0.4888 (2)	0.0523 (7)
C14	0.0237 (4)	0.4466 (2)	0.3894 (2)	0.0712 (9)
H14	−0.0821	0.4332	0.3217	0.085*
C15	0.1116 (5)	0.5081 (2)	0.3928 (2)	0.0775 (10)
H15	0.0667	0.5352	0.3268	0.093*
C16	0.2709 (4)	0.53257 (17)	0.4943 (2)	0.0600 (7)
C17	0.3695 (5)	0.59590 (19)	0.5046 (3)	0.0785 (10)
H17	0.3296	0.6257	0.4415	0.094*
C18	0.5209 (5)	0.61432 (19)	0.6043 (3)	0.0812 (10)
H18	0.5865	0.6558	0.6099	0.097*
C19	0.5781 (4)	0.57061 (14)	0.6991 (3)	0.0577 (7)
H19	0.6827	0.5836	0.7678	0.069*
C20	0.3383 (3)	0.49073 (13)	0.59409 (19)	0.0406 (5)
C21	0.2485 (3)	0.42380 (14)	0.59078 (19)	0.0391 (5)

	U11	U22	U33	U12	U13	U23
Ni1	0.02516 (17)	0.02713 (17)	0.02261 (17)	0.00032 (8)	0.01370 (14)	0.00058 (9)
O1	0.0485 (9)	0.0309 (8)	0.0463 (9)	−0.0124 (6)	0.0330 (8)	−0.0050 (6)
O1W	0.0337 (8)	0.0273 (7)	0.0319 (8)	−0.0008 (5)	0.0196 (7)	−0.0031 (6)
O2	0.0250 (8)	0.0409 (9)	0.0475 (10)	0.0004 (6)	0.0117 (8)	−0.0029 (7)
O2W	0.0397 (8)	0.0405 (8)	0.0361 (9)	0.0052 (6)	0.0228 (8)	−0.0012 (6)
O3	0.0311 (7)	0.0347 (7)	0.0257 (7)	0.0014 (5)	0.0165 (7)	−0.0032 (6)
O4	0.0298 (8)	0.0577 (10)	0.0384 (9)	0.0097 (7)	0.0130 (7)	−0.0155 (8)
N1	0.0280 (9)	0.0324 (9)	0.0272 (9)	−0.0026 (6)	0.0168 (8)	−0.0065 (7)
N2	0.0222 (8)	0.0463 (10)	0.0297 (9)	−0.0029 (7)	0.0121 (8)	−0.0118 (8)
N3	0.0301 (9)	0.0417 (10)	0.0281 (9)	0.0000 (7)	0.0181 (8)	−0.0045 (7)
N5	0.0483 (11)	0.0373 (10)	0.0342 (10)	0.0045 (8)	0.0250 (10)	0.0062 (8)
C1	0.0247 (10)	0.0249 (9)	0.0250 (10)	−0.0008 (7)	0.0141 (9)	0.0011 (7)
C2	0.0266 (10)	0.0275 (10)	0.0249 (10)	0.0023 (7)	0.0142 (9)	0.0004 (8)
C3	0.0238 (9)	0.0356 (11)	0.0280 (10)	0.0020 (8)	0.0150 (9)	−0.0013 (8)
C4	0.0247 (9)	0.0324 (10)	0.0234 (10)	−0.0004 (7)	0.0123 (9)	−0.0004 (8)
C5	0.0273 (9)	0.0259 (9)	0.0253 (10)	0.0003 (7)	0.0167 (9)	0.0006 (8)
C6	0.0227 (9)	0.0301 (10)	0.0306 (11)	−0.0013 (7)	0.0175 (9)	−0.0022 (8)
C7	0.0290 (11)	0.0405 (12)	0.0309 (11)	−0.0045 (8)	0.0159 (10)	−0.0123 (9)
C8	0.0283 (10)	0.0314 (11)	0.0331 (11)	−0.0057 (8)	0.0212 (9)	−0.0058 (8)
C9	0.0251 (10)	0.0316 (10)	0.0296 (11)	−0.0026 (8)	0.0160 (9)	−0.0027 (8)
C10	0.0447 (13)	0.0568 (15)	0.0428 (13)	−0.0148 (11)	0.0311 (12)	−0.0131 (11)
C11	0.0558 (16)	0.084 (2)	0.0632 (19)	−0.0333 (15)	0.0437 (16)	−0.0301 (16)
C12	0.0387 (14)	0.091 (2)	0.0433 (16)	−0.0135 (13)	0.0195 (13)	−0.0268 (15)
C13	0.0389 (13)	0.0677 (17)	0.0340 (13)	0.0058 (12)	0.0152 (12)	−0.0118 (12)
C14	0.0542 (18)	0.091 (2)	0.0265 (14)	0.0131 (15)	0.0055 (14)	−0.0051 (13)
C15	0.085 (2)	0.079 (2)	0.0324 (15)	0.0178 (18)	0.0202 (16)	0.0141 (14)
C16	0.0776 (19)	0.0562 (16)	0.0387 (14)	0.0174 (14)	0.0330 (15)	0.0119 (12)
C17	0.110 (3)	0.0605 (19)	0.056 (2)	0.0062 (18)	0.048 (2)	0.0265 (15)
C18	0.112 (3)	0.0601 (19)	0.069 (2)	−0.0128 (18)	0.056 (2)	0.0185 (16)
C19	0.0712 (19)	0.0452 (15)	0.0536 (17)	−0.0087 (12)	0.0378 (16)	0.0068 (11)
C20	0.0473 (13)	0.0392 (12)	0.0311 (12)	0.0119 (9)	0.0227 (11)	0.0060 (9)
C21	0.0332 (12)	0.0501 (13)	0.0249 (11)	0.0109 (9)	0.0140 (10)	−0.0035 (9)

Ni1—O3i	2.0241 (14)	C2—C9	1.502 (3)
Ni1—N5	2.0715 (19)	C3—C4	1.386 (3)
Ni1—N3	2.0828 (18)	C3—H3	0.9300
Ni1—N1	2.0994 (16)	C4—C5	1.399 (3)
Ni1—O1W	2.1098 (15)	C5—C6	1.395 (3)
Ni1—O2W	2.1507 (15)	C6—H6	0.9300
O1—C8	1.274 (2)	C7—H7	0.9300
O1W—H1W	0.8402	C10—C11	1.404 (3)
O1W—H2W	0.8401	C10—H10	0.9300
O2—C8	1.233 (2)	C11—C12	1.362 (4)
O2W—H3W	0.8400	C11—H11	0.9300
O2W—H4W	0.8400	C12—C13	1.392 (4)
O3—C9	1.265 (2)	C12—H12	0.9300
O3—Ni1ii	2.0241 (14)	C13—C21	1.404 (3)
O4—C9	1.244 (2)	C13—C14	1.441 (4)
N1—C7	1.323 (3)	C14—C15	1.345 (5)
N1—C5	1.396 (3)	C14—H14	0.9300
N2—C7	1.335 (3)	C15—C16	1.418 (4)
N2—C4	1.376 (3)	C15—H15	0.9300
N2—H2	0.8600	C16—C17	1.400 (5)
N3—C10	1.319 (3)	C16—C20	1.413 (3)
N3—C21	1.364 (3)	C17—C18	1.346 (5)
N5—C19	1.334 (3)	C17—H17	0.9300
N5—C20	1.350 (3)	C18—C19	1.393 (4)
C1—C6	1.381 (3)	C18—H18	0.9300
C1—C2	1.417 (3)	C19—H19	0.9300
C1—C8	1.510 (3)	C20—C21	1.431 (3)
C2—C3	1.384 (3)
O3i—Ni1—N5	174.88 (7)	C1—C6—C5	118.45 (17)
O3i—Ni1—N3	94.83 (7)	C1—C6—H6	120.8
N5—Ni1—N3	80.31 (8)	C5—C6—H6	120.8
O3i—Ni1—N1	91.71 (6)	N1—C7—N2	113.37 (18)
N5—Ni1—N1	90.62 (8)	N1—C7—H7	123.3
N3—Ni1—N1	98.62 (7)	N2—C7—H7	123.3
O3i—Ni1—O1W	92.03 (6)	O2—C8—O1	124.26 (18)
N5—Ni1—O1W	92.56 (7)	O2—C8—C1	118.08 (18)
N3—Ni1—O1W	169.42 (6)	O1—C8—C1	117.48 (17)
N1—Ni1—O1W	89.19 (6)	O4—C9—O3	125.86 (19)
O3i—Ni1—O2W	85.71 (6)	O4—C9—C2	118.28 (17)
N5—Ni1—O2W	92.07 (7)	O3—C9—C2	115.85 (16)
N3—Ni1—O2W	83.24 (7)	N3—C10—C11	122.1 (2)
N1—Ni1—O2W	176.95 (6)	N3—C10—H10	119.0
O1W—Ni1—O2W	89.27 (6)	C11—C10—H10	119.0
Ni1—O1W—H1W	109.5	C12—C11—C10	119.2 (3)
Ni1—O1W—H2W	98.3	C12—C11—H11	120.4
H1W—O1W—H2W	109.2	C10—C11—H11	120.4
Ni1—O2W—H3W	107.8	C11—C12—C13	120.7 (2)
Ni1—O2W—H4W	102.0	C11—C12—H12	119.6
H3W—O2W—H4W	110.4	C13—C12—H12	119.6
C9—O3—Ni1ii	126.97 (12)	C12—C13—C21	116.6 (2)
C7—N1—C5	104.75 (16)	C12—C13—C14	124.8 (3)
C7—N1—Ni1	122.19 (14)	C21—C13—C14	118.6 (3)
C5—N1—Ni1	133.06 (13)	C15—C14—C13	121.1 (3)
C7—N2—C4	107.40 (17)	C15—C14—H14	119.5
C7—N2—H2	126.3	C13—C14—H14	119.5
C4—N2—H2	126.3	C14—C15—C16	121.8 (3)
C10—N3—C21	118.60 (19)	C14—C15—H15	119.1
C10—N3—Ni1	129.35 (15)	C16—C15—H15	119.1
C21—N3—Ni1	112.04 (15)	C17—C16—C15	125.1 (3)
C19—N5—C20	118.7 (2)	C17—C16—C20	116.3 (3)
C19—N5—Ni1	128.25 (18)	C15—C16—C20	118.6 (3)
C20—N5—Ni1	112.85 (15)	C18—C17—C16	121.1 (3)
C6—C1—C2	121.47 (17)	C18—C17—H17	119.5
C6—C1—C8	116.26 (16)	C16—C17—H17	119.5
C2—C1—C8	122.22 (17)	C17—C18—C19	119.2 (3)
C3—C2—C1	120.47 (18)	C17—C18—H18	120.4
C3—C2—C9	118.32 (17)	C19—C18—H18	120.4
C1—C2—C9	121.09 (16)	N5—C19—C18	122.2 (3)
C4—C3—C2	117.13 (18)	N5—C19—H19	118.9
C4—C3—H3	121.4	C18—C19—H19	118.9
C2—C3—H3	121.4	N5—C20—C16	122.5 (2)
N2—C4—C3	131.06 (18)	N5—C20—C21	117.47 (19)
N2—C4—C5	105.66 (17)	C16—C20—C21	120.0 (2)
C3—C4—C5	123.27 (18)	N3—C21—C13	122.9 (2)
N1—C5—C6	131.99 (17)	N3—C21—C20	117.3 (2)
N1—C5—C4	108.82 (16)	C13—C21—C20	119.8 (2)
C6—C5—C4	119.16 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1iii	0.84	1.90	2.710 (2)	163
O1W—H2W···O4i	0.84	1.76	2.584 (2)	165
O2W—H3W···O1iii	0.84	1.87	2.703 (2)	169
O2W—H4W···O1i	0.84	2.11	2.932 (2)	165
N2—H2···O2iv	0.86	2.00	2.739 (2)	144
N2—H2···O1iv	0.86	2.54	3.355 (2)	159
C10—H10···O2i	0.93	2.56	3.346 (8)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1i	0.84	1.90	2.710 (2)	163
O1W—H2W⋯O4ii	0.84	1.76	2.584 (2)	165
O2W—H3W⋯O1i	0.84	1.87	2.703 (2)	169
O2W—H4W⋯O1ii	0.84	2.11	2.932 (2)	165
N2—H2⋯O2iii	0.86	2.00	2.739 (2)	144
N2—H2⋯O1iii	0.86	2.54	3.355 (2)	159
C10—H10⋯O2ii	0.93	2.56	3.346 (8)	143

Symmetry codes: (i) ; (ii) ; (iii) .